Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine

A technology of methoxymethylaniline and methoxymethyl, which is applied in the field of new-type condensation synthesis and can solve problems such as unsatisfactory purity results

Active Publication Date: 2017-08-18
WELLA OPERATIONS US LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this synthetic route is unsatisfactory in terms of purity results and also produces some by-products such as aminobiphenyl

Method used

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  • Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
  • Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
  • Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine

Examples

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Embodiment

[0064] The following are non-limiting examples of compositions of the invention. These examples are given for the purpose of illustration only and are not to be construed as limiting the invention, since many variations thereof are possible without departing from the spirit and scope of the invention, which will be recognized by ordinary skill in the art recognized by personnel. All concentrations are listed in percent by weight unless specifically stated otherwise.

[0065] A) Preparation of 2-methoxymethylaniline (II) starting from 2-nitro-benzyl alcohol (VI)

[0066] A 1 ) to synthesize 2-nitro-methoxymethyl-benzene (VII)

[0067] The following emulsions have been prepared:

[0068] 12.0kg 2-nitro-benzyl alcohol 60l toluene 12l water 61l Benzyl-tributyl-ammonium chloride 9.4kg sodium hydroxide

[0069] A solution of 12.8 kg of dimethyl sulfate in 12 l of toluene was added to the above emulsion at about 20° C. over a period o...

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Abstract

A telescoping process for the preparation of 2-methoxymethyl-p-phenylenediamine, a cosmetically acceptable salt thereof, or mixture thereof. The process according to the present invention is a particularly cost effective process in that it avoids sophisticated chemical steps which requires special equipment or expensive catalysts and in that it comprises a recycling step of one of the starting materials, namely 2-methoxymethylaniline.

Description

[0001] field of invention [0002] The present invention relates to a novel telescoping synthesis of 2-methoxymethyl-p-phenylenediamine or salts thereof according to formula (I). This compound is known in the industry as a hypoallergenic primary dye precursor for use in oxidative hair dye compositions as an alternative to traditional p-phenylenediamine or p-toluenediamine dye precursors. [0003] [0004] Background of the invention [0005] p-Phenylenediamine derivatives are important precursors for oxidative hair coloring. They are often used to create dark shades. P-phenylenediamine derivatives have been used for decades in hair coloring. Among the p-phenylenediamine derivatives, a particularly favorable candidate, namely 2-methoxymethyl-p-phenylenediamine, has been identified. Such dye precursors are particularly advantageous because they are typically characterized by a lower sensitization potential than conventional p-phenylenediamine or p-toluenediamine dye precurs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/76
CPCC07C213/02C07C245/08C07C245/20C07C245/24C07C217/76Y02P20/582C07C209/24
Inventor 海克·格特鲁德·阿贝尔阿明·奥桑马库斯·施佩克巴切尔英戈·赖因霍尔德·韦伯加里·史蒂文·加雷特
Owner WELLA OPERATIONS US LLC
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